6-Amidino-1-carbamoylmethyl-2-naphthyl 4-nitrobenzoate.hydrochloride → 6-Amidino-1-carbamoylmethyl-2-naphthyl 4-aminobenzoate.dihydrochloride

HRID 1419226Notes

Reaction equation

HRID 1419226 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22](=[NH:24])[NH2:23])[CH:18]=3)[C:13]=2[CH2:25][C:26](=[O:28])[NH2:27])=[O:10])=[CH:7][CH:6]=1)([O-])=O>[C].[Pd].CN(C=O)C>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22](=[NH:23])[NH2:24])[CH:18]=3)[C:13]=2[CH2:25][C:26](=[O:28])[NH2:27])=[O:10])=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 701312286-Amidino-1-carbamoylmethyl-2-naphthyl 4-nitrobenzoate.hydrochloride

Product 1

HCID 701325966-Amidino-1-carbamoylmethyl-2-naphthyl 4-aminobenzoate.dihydrochlorideYield 188.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To 600 mg of 6-amidino-1-carbamoylmethyl-2-naphthyl 4-nitrobenzoate.hydrochloride were added 10 ml of anhydrous DMF and 100 mg of 10% palladium carbon, and catalytic reduction was effected at room temperature for 24 hours. Then, insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. To the residue was added 15 ml of methanol, and, furthermore, 350 μl of concentrated hydrochloric acid was added with stirring under cooling with ice. Then, the resulting solution was added dropwise to 200 ml of acetone, followed by stirring for 1 hour under cooling with ice. Then, the precipitate was collected by filtration to obtain 572.7 mg of the desired product.

Workup

  1. filtrationThen, insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added 15 ml of methanol
  4. additionfurthermore, 350 μl of concentrated hydrochloric acid was added
  5. temperatureunder cooling with ice
  6. additionThen, the resulting solution was added dropwise to 200 ml of acetone
  7. stirringby stirring for 1 hour
  8. temperatureunder cooling with ice
  9. filtrationThen, the precipitate was collected by filtration

Sources & evidence

ORD record
ord-5d8cdbd579214dfe9cd1f14c441aa46d
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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